A new class of biosourced bisphenols for applications in polymer chemistry

Research scientists from INRA and AgroParisTech have developed a bio-catalytic method using plant biomass to produce a range of compounds that could be proposed as replacements for bisphenol A and whose use properties can be tuned as required.

Une nouvelle classe de  bisphénols  biosourcés pour des applications en  CHIMIE  des polymères © Nikkytok - Fotolia
Updated on 06/20/2014
Published on 06/20/2014

The controversial use of bisphenol A

 

Bisphenol compounds are included in the composition of different polymers (polycarbonates, polyesters, polyurethanes, etc.).  Inexpensive, they have the advantage of endowing these matrices with thermomechanical, plasticising and/or antioxidant properties, which are notably sought for packaging applications.  Their principal drawback is their proven toxicity to humans and more globally to the environment.  In the long term, changes to the REACH regulations may ban their use, and particularly that of bisphenol A (BPA) in products destined to come into contact with humans (packaging, health sectors, etc.).

 

Using plant phenols for the ecological production of a range of replacement compounds with tunable properties

 

The methodology developed by the scientists specifically uses "raw materials" of plant origin: (1) platform molecules resulting from the conversion of cell wall polysaccharides, (2) ferulic acid from lignocellulose, and (3) glycerol. The first two stages of this synthesis are chemical transformations that are widely applied in industry and have a limited environmental impact. The third stage is a bio-catalytic condensation process which involves a commercial lipase.  This process requires neither the use of chemical protection/deprotection reactions, nor that of solvents.  The method is highly flexible because it enables the condensation of a ferulic acid derivative with different compounds (such as polyols or polyamines) in order to produce a broader range of compounds with tunable properties.

The new bisphenolic compounds thus obtained exhibit excellent thermal stability up to a temperature of 250 °C. They can be used as antioxidants/anti-free radical substances and/or as biosourced plasticisers which display no endocrine disrupting activity.

 

An innovative application: the synthesis of new biosourced "plastic materials".

 

Because of their properties, these new bisphenols could be used in replacement of bisphenol A for the manufacture of food packaging.  They could also be employed as monomers for the synthesis of new polyesters or polyurethanes, etc., or - after functionalisation - as monomers for the synthesis of polyamides or polyolefins. The range of potential compounds or applications is therefore considerable.

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For further information

  • Pion Florian; Ducrot Paul-Henri; Allais Florent « Biorenewable copolyesters derived from a bio- based carbohydrate and lignin » Polymer Preprints 2012, 53(2), 264
  • Pion Florian; Reano Armando F.; Ducrot Paul-Henri; Allais, Florent «  Chemo-enzymatic preparation of new bio-based bis- and trisphenols : new versatile building blocks for polymer chemistry »  RSC Adv. 2013, 3, 8988-8997
  • Pion Florian; Ducrot Paul-Henri; Allais Florent « Renewable alternating aliphatic-aromatic copolyesters derived from bio-based ferulic acid, diols and diacids: sustainable polymers with tunable thermal properties » Macromol. Chem. Phys. 2014, 431-439